ES2198102T3 - Nuevos derivados hidroxi de la tilosina y procedimiento para su preparacion. - Google Patents

Nuevos derivados hidroxi de la tilosina y procedimiento para su preparacion.

Info

Publication number: ES2198102T3
Authority: ES; Spain
Prior art keywords: line; double bond; noh; mycarosyl; och
Prior art date: 1998-09-10
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES99117654T

Other languages

English (en)

Spanish (es)

Inventor

Amalija Narandja

Nevenka Lopotar

Zoran Mandic

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pliva Farmaceutika dd

Original Assignee

Pliva Farmaceutska Kemijska Prehrambena I Kozmeticka Industrija dd

Pliva Farmaceutska Industrija dd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-09-10

Filing date

1999-09-07

Publication date

2004-01-16

1999-09-07 Application filed by Pliva Farmaceutska Kemijska Prehrambena I Kozmeticka Industrija dd, Pliva Farmaceutska Industrija dd filed Critical Pliva Farmaceutska Kemijska Prehrambena I Kozmeticka Industrija dd

2004-01-16 Application granted granted Critical

2004-01-16 Publication of ES2198102T3 publication Critical patent/ES2198102T3/es

2019-09-07 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical class [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 32
238000006243 chemical reaction Methods 0.000 claims abstract description 9
238000006146 oximation reaction Methods 0.000 claims abstract description 8
239000004182 Tylosin Substances 0.000 claims abstract description 7
229960004059 tylosin Drugs 0.000 claims abstract description 7
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 6
WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 claims abstract description 6
229930194936 Tylosin Natural products 0.000 claims abstract description 5
230000007062 hydrolysis Effects 0.000 claims abstract description 5
235000019375 tylosin Nutrition 0.000 claims abstract description 5
238000007254 oxidation reaction Methods 0.000 claims abstract description 4
230000003197 catalytic effect Effects 0.000 claims abstract 2
230000003647 oxidation Effects 0.000 claims abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
150000001204 N-oxides Chemical class 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
235000019270 ammonium chloride Nutrition 0.000 claims description 3
239000010439 graphite Substances 0.000 claims description 3
229910002804 graphite Inorganic materials 0.000 claims description 3
239000008055 phosphate buffer solution Substances 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
239000003120 macrolide antibiotic agent Substances 0.000 abstract description 2
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 abstract 1
229940125797 compound 12 Drugs 0.000 abstract 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 59
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 9
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000284 extract Substances 0.000 description 6
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
150000002923 oximes Chemical class 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000000605 extraction Methods 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
229940125904 compound 1 Drugs 0.000 description 4
244000257039 Duranta repens Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
238000002955 isolation Methods 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
241001459693 Dipterocarpus zeylanicus Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
235000018734 Sambucus australis Nutrition 0.000 description 2
244000180577 Sambucus australis Species 0.000 description 2
238000013019 agitation Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
KQGNNBDIKMWWJS-UHFFFAOYSA-N [OH-].[NH4+].C=CO Chemical compound [OH-].[NH4+].C=CO KQGNNBDIKMWWJS-UHFFFAOYSA-N 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
GHQPBDDZGPAVJP-UHFFFAOYSA-N azanium;methanol;hydroxide Chemical compound N.O.OC GHQPBDDZGPAVJP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Genetics & Genomics (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Seasonings (AREA)
Steroid Compounds (AREA)

ES99117654T 1998-09-10 1999-09-07 Nuevos derivados hidroxi de la tilosina y procedimiento para su preparacion. Expired - Lifetime ES2198102T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HR980496A HRP980496B1 (en)	1998-09-10	1998-09-10	New thilozine hydroxy derivatives and a process for the preparation thereof
HR980496		1998-09-10

Publications (1)

Publication Number	Publication Date
ES2198102T3 true ES2198102T3 (es)	2004-01-16

Family

ID=10946806

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES99117654T Expired - Lifetime ES2198102T3 (es)	1998-09-10	1999-09-07	Nuevos derivados hidroxi de la tilosina y procedimiento para su preparacion.

Country Status (19)

Country	Link
US (1)	US6211348B1 (de)
EP (1)	EP0985679B8 (de)
JP (1)	JP2000086691A (de)
CN (1)	CN1150202C (de)
AT (1)	ATE238331T1 (de)
BG (1)	BG64561B1 (de)
CA (1)	CA2281496C (de)
CZ (1)	CZ294935B6 (de)
DE (1)	DE69907101T2 (de)
DK (1)	DK0985679T3 (de)
ES (1)	ES2198102T3 (de)
HR (1)	HRP980496B1 (de)
HU (1)	HUP9903063A2 (de)
NO (1)	NO312839B1 (de)
PL (1)	PL195483B1 (de)
RU (1)	RU2220149C2 (de)
SI (1)	SI0985679T1 (de)
SK (1)	SK284841B6 (de)
UA (1)	UA66355C2 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7247617B2 (en)	2004-07-13	2007-07-24	Kosan Biosciences Incorporated	Sixteen-member macrolide antiinfective agents
WO2006073172A1 (ja) *	2005-01-07	2006-07-13	Meiji Seika Kaisha, Ltd.	12-オキシ-13-アミノ含有16員環マクロライド誘導体及びその製造法
FR2891835B1 (fr) *	2005-10-11	2007-12-14	Alchimer Sa	Procede de modification de surfaces de polymeres, notamment d'hydroxylation de surfaces de polymeres, et produits tels qu'obtenus
CN117510561B (zh) *	2023-11-30	2024-04-02	中国农业科学院饲料研究所	一种泰乐菌素衍生物及其制备方法与应用

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BG32649A1 (en) *	1981-03-26	1982-09-15	Kirov	Method for obtaining of antibiotic tilozine
AU551142B2 (en) *	1981-07-09	1986-04-17	Zaidan Hojin Biseibutsu Kagaku Kenkyukai	Tylosin derivatives
US4454314A (en) *	1982-08-02	1984-06-12	Pfizer Inc.	Antibacterial mycaminosyl tylonolide and related macrolide derivatives
EP0265735B1 (de) *	1986-10-22	1991-01-16	Ferag AG	Verfahren und Vorrichtung zum Übernehmen von gefalzten Druckereierzeugnissen von Druckmaschinen
SI8710674B (sl) *	1987-04-14	1998-06-30	Pliva	Postopek za pripravo 10,11,12,13-tetrahidro derivatov tilozina
DE4200145A1 (de) *	1992-01-07	1993-07-08	Kali Chemie Pharma Gmbh	7,10-epoxy-oxacyclododecan-derivate, verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JP3063943B2 (ja) *	1992-02-26	2000-07-12	明治製菓株式会社	血漿中において抗菌活性の持続する新規１６員環マクロリド誘導体及びその合成中間体とそれらの製造法
HRP950449A2 (en) *	1995-08-14	1997-12-31	Nevenka Lopotar	Derivatives of 12, 13-epoxy-tylosin and processes of manufacture thereof
HRP960509A2 (en) *	1996-10-30	1998-06-30	Pliva Pharm & Chem Works	Novel polyhydro tylosin derivatives and a process for the preparation thereof

1998
- 1998-09-10 HR HR980496A patent/HRP980496B1/xx not_active IP Right Cessation
1999
- 1999-09-06 CZ CZ19993154A patent/CZ294935B6/cs not_active IP Right Cessation
- 1999-09-07 DK DK99117654T patent/DK0985679T3/da active
- 1999-09-07 SI SI9930319T patent/SI0985679T1/xx unknown
- 1999-09-07 AT AT99117654T patent/ATE238331T1/de not_active IP Right Cessation
- 1999-09-07 ES ES99117654T patent/ES2198102T3/es not_active Expired - Lifetime
- 1999-09-07 DE DE69907101T patent/DE69907101T2/de not_active Expired - Lifetime
- 1999-09-07 EP EP99117654A patent/EP0985679B8/de not_active Expired - Lifetime
- 1999-09-09 NO NO19994366A patent/NO312839B1/no unknown
- 1999-09-09 RU RU99119585/04A patent/RU2220149C2/ru not_active IP Right Cessation
- 1999-09-09 UA UA99095030A patent/UA66355C2/uk unknown
- 1999-09-09 CA CA002281496A patent/CA2281496C/en not_active Expired - Fee Related
- 1999-09-10 US US09/393,322 patent/US6211348B1/en not_active Expired - Fee Related
- 1999-09-10 CN CNB991220617A patent/CN1150202C/zh not_active Expired - Fee Related
- 1999-09-10 HU HU9903063A patent/HUP9903063A2/hu unknown
- 1999-09-10 BG BG103726A patent/BG64561B1/bg unknown
- 1999-09-10 JP JP11256906A patent/JP2000086691A/ja active Pending
- 1999-09-10 SK SK1241-99A patent/SK284841B6/sk unknown
- 1999-09-10 PL PL335362A patent/PL195483B1/pl unknown

Also Published As

Publication number	Publication date
UA66355C2 (en)	2004-05-17
DE69907101T2 (de)	2004-04-08
HRP980496A2 (en)	2000-04-30
HRP980496B1 (en)	2007-03-31
RU2220149C2 (ru)	2003-12-27
HUP9903063A2 (hu)	2000-03-28
DK0985679T3 (da)	2003-08-11
NO994366L (no)	2000-03-13
CN1150202C (zh)	2004-05-19
CN1250054A (zh)	2000-04-12
JP2000086691A (ja)	2000-03-28
NO312839B1 (no)	2002-07-08
DE69907101D1 (de)	2003-05-28
CZ294935B6 (cs)	2005-04-13
CZ315499A3 (cs)	2000-04-12
NO994366D0 (no)	1999-09-09
CA2281496A1 (en)	2000-03-10
SI0985679T1 (en)	2003-10-31
EP0985679B8 (de)	2003-09-03
EP0985679A1 (de)	2000-03-15
BG103726A (en)	2000-12-29
ATE238331T1 (de)	2003-05-15
PL335362A1 (en)	2000-03-13
EP0985679B1 (de)	2003-04-23
BG64561B1 (bg)	2005-07-29
US6211348B1 (en)	2001-04-03
CA2281496C (en)	2005-11-01
SK124199A3 (en)	2000-12-11
SK284841B6 (sk)	2005-12-01
PL195483B1 (pl)	2007-09-28

Publication	Publication Date	Title
EP0109253B1 (de)	1987-10-14	Epi-Derivat von Azahomoerythromycin A und Zwischenprodukte
RU2045533C1 (ru)	1995-10-10	О-метильные производные азитромицина а, обладающие антибактериальной активностью, азитромицины в качестве промежуточных соединений для получения о-метильных производных азитромицина а и способ получения о-метильных производных азитромицина а
EP0287082B1 (de)	1994-03-23	Tylosin- und 10,11,12,13-Tetrahydrotylosin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung in pharmazeutischen Zusammensetzungen und bei deren Herstellung
ES2198102T3 (es)	2004-01-16	Nuevos derivados hidroxi de la tilosina y procedimiento para su preparacion.
EP0410433A2 (de)	1991-01-30	Tylosin-Derivate
US4585759A (en)	1986-04-29	Antibacterial derivatives of a neutral macrolide
DK152133B (da)	1988-02-01	Analogifremgangsmaade til fremstilling af oleandomycinderivater eller farmaceutisk acceptable syreadditionssalte deraf
US5922684A (en)	1999-07-13	Polyhydro derivatives of tylosine and process for their preparation
HU180298B (en)	1983-02-28	Process for preparing new glycoside compunds
US5688924A (en)	1997-11-18	Derivatives of 12,13-Epoxy-tylosin and processes of manufacture thereof
DE3009910C2 (de)	1986-05-22	3',4'-Diepi-4'-O-methyl-daunorubicin und -doxorubicin, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
ES2198302T3 (es)	2004-02-01	Derivados de 3-desoxi-desmicosina y su procedimiento de preparacion.
CA1250284A (en)	1989-02-21	Antibacterial epimeric azahomoerythromycin a derivative and production thereof
Boluda et al.	2009	Semisynthesis of justicidone and a 1, 2-quinone lignan. Cytotoxic activity of some natural and synthetic lignans
SK278717B6 (sk)	1998-01-14	Deriváty 10, 11, 12, 13-tetrahydrodesmykozínu, spô